Trimethyl borate → (5-Cyano-2-Methoxyphenyl)Boronic Acid

HRID 1622084

反応式

HRID 1622084 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].C([Mg]Cl)(C)C.[B:17](OC)([O:20]C)[O:18]C>O1CCCC1>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([B:17]([OH:20])[OH:18])[CH:3]=1)#[N:6]

参加物

5

反応物 3

HCID 8470Trimethyl borateHCID 7360493-Bromo-4-methoxybenzonitrileHCID 178418918HCID 178418918、化合物

生成物 1

HCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic Acid収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

3-Bromo-4-methoxybenzonitrile (3.0 g, 14.2 mmol, 1.0 eq) was dissolved in anhydrous tetrahydrofuran (10 mLs). The solution cooled at −10° C. and stirred while isopropylmagnesium chloride (17.7 mmol, 8.8 mLs, 2.0 M in THF, 1.25 eq.) was added. The mixture was stirred for 1 hour and then trimethyl borate (1.87 g, 17.7 mmol, 2.0 mL) was added dropwise. The mixture was allowed to warm slowly to room temperature for 1 hour. The solvent was evaporated and the residue was partitioned between 5% citric acid and ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to a minimum volume under reduced pressure. The residue was recrystallized from hexanes to give 5-cyano-2-methoxybenzeneboronic acid (2.48 g, 99%) as a fluffy white powder.

後処理

  1. additionwas added
  2. temperatureto warm slowly to room temperature for 1 hour
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between 5% citric acid and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated to a minimum volume under reduced pressure
  9. customThe residue was recrystallized from hexanes

出典と根拠

ORDレコード
ord-630c3da5fcde423d819b3b8a7bec6e3c
出典データセット
uspto-grants-2014_07
特許番号
US08778625B2

関連ノート

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